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Star anise (Illicium verum)


Illicium verum
Synonyms / Common Names / Related Terms
Anice stellato, anis de la Chine (French), anis estrellado, anise étoilé (French), anise stars, aniseed, Anisi stellati fructus, ba chio, badain, badaine, badian, badiana, ba(ht) g(h)ok, bart gok, bunga lawang, Chinese anise, Chinese star anise, eight-horned anise, eight horns, I. anisatum, Illicium anisatum L (Japanese star anise), Illicium verum, Illicium religiosum, Illicium verum Hook f, pa-chiao, pak kok, peh kah, star anise, sternanis, Tamiflu®.

Note: Do not confuse Japanese star anise (Illicium anisatum) with Chinese star anise (Illicium verum). Japanese star anise has been observed to cause serious adverse effects in case studies.,,,

Mechanism of Action

Pharmacology:

  • Constituents: Star anise contains anethole, which is the same ingredient that gives the anise (Pimpinella anium) its distinctive licorice flavor. One cell line study suggested that anethole, a componet of star anise, may possess antimicrobial properties effective against bacteria, yeast and fungal strains.5
  • Star anise contains anethole, cinnamaldehyde, 0-methoxycinnamaldehyde, p-methoxy-cinnamaldehyde, cinnamic acid, p- methoxycinnamaldehyde, cinnamyl alcohol, trans-anethole, beta-caryophyllene, citronellol, estragole, eugenol methyl ether, myrcene, p-methoxy phenylacetone, terpinen-4-ol gamma-terpinene, anisaldehyde, astragalin, kaempferol, kaempferol-3-O-alpha-L-galactoside, kaempferol-3-O- beta -D-rutinoside, quercetin, quercetin-3-O-alpha-L-galactoside, quercetin-3-O-alpha-L-rhamnoside, quercetin-3-O-alpha-D-glucoside, quercetin-3-O-alpha-D-rutinoside, quercetin-3-O-alpha-D-xyloside, benzoic acid-4- beta -D-glucoside, caffeic acid, p-coumaric acid, and cineol. It also contains neurotropic sesquiterpenoids, veranisatins A, B and C, phenylpropanoids, two lignans.9,3,10,11,12
  • In one study the content of anethole in the fruit of star anise (Illicium verum) was more than 4.5%.13
  • A racemic mixture of phenylpropanoids, [1-(4'-methoxyphenyl)-(1 R,2 S and 1 S,2 R)-propanediol and 1-(4'-methoxyphenyl)-(1 R,2 R and 1 S,2 S)- propanediol ], along with two known phenylpropanoid glucosides, [1-(4'-methoxyphenyl)-(1 S,2 R)- propan-1-ol 2-O-beta-D-glucopyranoside and 1-(4'-methoxyphenyl)-(1 R,2 S)-propan-1-ol 2-O-beta-D- glucopyranoside], and two new phenylpropanoid glucosides, [1-(4'-methoxyphenyl)-(1 S,2 S)-propan-1-ol 2- O-beta- D-glucopyranoside and 1-(4'-methoxyphenyl)-(1 R,2 R)-propan-1-ol 2-O-beta-D- glucopyranoside ] were isolated from Illicium verum.
  • Nine new phenylpropanoids (2-7, 10, 12, and 14) and two compounds representing novel structural classes of 7-O-8' and 7-O-8'.8-O-7' lignans (8 and 9, respectively) have been isolated from Illicium verum. Most of these compounds appear to be biogenetically derived from threo-anethole glycol.11
  • Three new neurotropic sesquiterpenoids, veranisatins A, B and C, were isolated from star anise (Illicium verum Hook. fil. Illiciaceae). Veranisatins showed convulsion and lethal toxicity in mice by mouth at a dose of 3mg/kg, and at lower doses they caused hypothermia. Veranisatin A and the related compound, anisatin, were tested for the other pharmacological activities such as locomotor activity and analgesic effect. Both compounds decreased the locomotion enhanced by methamphetamine at oral doses of 0.1 and 0.03mg/kg, respectively, and demonstrated the analgesia on acetic acid-induced writhing and tail pressure pain at almost similar doses.3
  • Illicium verum has shown to have inhibitory activity on the tube-like formation induced by human umbilical venous endothelial cells in vitro 8.
  • One new phenylpropanoid glucoside (3), along with one known phenylpropanoid (1), and one known alkyl glucoside (2) were isolated from the fruits of Illicium verum.14
  • Analgesic effects: Three new neurotropic sesquiterpenoids, veranisatins A, B and C, were isolated from star anise (Illicium verum Hook. fil. Illiciaceae). Veranisatins showed convulsion and lethal toxicity in mice by mouth at a dose of 3mg/kg, and at lower doses they caused hypothermia. Veranisatin A and the related compound, anisatin, were tested for the other pharmacological activities such as locomotor activity and analgesic effect. Both compounds decreased the locomotion enhanced by methamphetamine at oral doses of 0.1 and 0.03mg/kg, respectively, and demonstrated the analgesia on acetic acid-induced writhing and tail pressure pain at almost similar doses.3
  • Antimicrobial activity: Illicium verum methanol extract was tested for its antibacterial activity against Porphyromonas gingivalis, Prevotella spp., Fusobacterium nucleatum, Capnocytophaga gingivalis, Veilonella parvula, Eikenella corrodens, Peptostreptococcus micros and Actinomyces odontolyticus. It was not found to be active though it had a particular good activity against E. corrodens.4
  • Star anise (Illicium verum Hook f) has been shown to possess potent antimicrobial properties. Chemical studies indicate that a major portion of this antimicrobial property is due to anethole present in the dried fruit. Studies with isolated anethole (compared with standard anethole) indicated that it is effective against bacteria, yeast and fungal strains.5
  • Antiviral properties: Shikimic acid, extracted from the pods (which wraps the seeds), is the starting ingredient of Tamiflu® (oseltamivir). Shikimic acid is a precursor for the aromatic amino acids phenylalanine and tyrosine, indole, and indole derivatives, tryptophan, many alkaloids and other aromatic metabolites, tannins, and lignin. Tamiflu® is an antiviral drug and the proposed mechanism of action of oseltamivir is inhibition of influenza virus neuraminidase with the possibility of alteration of virus particle aggregation and release.
  • Hepatic effects: A study of mice fed ethanol extracts of Illicium verum to determine the effects on liver enzymes found increased 7-ethoxycoumarin O-deethylase activity and an increase in microsomal and cytosolic epoxide hydratase.6,7
  • A compound isolated from Illicium verum, 1-(4'-methoxyphenyl)-(1 R,2 S and 1 S,2 R)-propanediol, exhibited the highest survival rate in a dose-dependent manner (100 % with a dose of 10mg/kg against 40 % for the control experiment) and showed a reduction of the plasma alanine aminotransferase (ALT) value on the in vivo assay model of septic shock induced by tumor necrosis factor (TNF)-alpha.15
  • Insecticidal effects: Illicium verum essential oil has insecticidal activities against the Japanese termite, Reticulitermes speratus Kolbe. At 2microL/L of air concentration there was 100% mortality within 2 days of treatment.1 Anethole, a constituent of IIicium verum has been reported to be toxic to German cockroaches Blattella germanica.2

Pharmacodynamics/Kinetics:

  • Insufficient available evidence.

References
  1. Park, I. K. and Shin, S. C. Fumigant activity of plant essential oils and components from garlic (Allium sativum) and clove bud (Eugenia caryophyllata) oils against the Japanese termite (Reticulitermes speratus Kolbe). J Agric Food Chem 6-1-2005;53(11):4388-4392. 15913300
  2. Chang, K. S. and Ahn, Y. J. Fumigant activity of (E)-anethole identified in Illicium verum fruit against Blattella germanica. Pest Manag Sci 2002;58(2):161-166. 11852640
  3. Nakamura, T., Okuyama, E., and Yamazaki, M. Neurotropic components from star anise (Illicium verum Hook. fil.). Chem Pharm Bull (Tokyo) 1996;44(10):1908-1914. 8904818
  4. Iauk, L., Lo Bue, A. M., Milazzo, I., Rapisarda, A., and Blandino, G. Antibacterial activity of medicinal plant extracts against periodontopathic bacteria. Phytother Res 2003;17(6):599-604. 12820224
  5. De, M., De, A. K., Sen, P., and Banerjee, A. B. Antimicrobial properties of star anise (Illicium verum Hook f). Phytother Res 2002;16(1):94-95. 11807977
  6. Hendrich, S. and Bjeldanes, L. F. Effects of dietary Schizandra chinensis, brussels sprouts and Illicium verum extracts on carcinogen metabolism systems in mouse liver. Food Chem Toxicol  1986;24(9):903-912. 3096852
  7. Hendrich, S. and Bjeldanes, L. F. Effects of dietary cabbage, Brussels sprouts, Illicium verum, Schizandra chinensis and alfalfa on the benzo[alpha]pyrene metabolic system in mouse liver. Food Chem Toxicol  1983;21(4):479-486. 6311701
  8. Nam, N. H., Kim, H. M., Bae, K. H., and Ahn, B. Z. Inhibitory effects of Vietnamese medicinal plants on tube-like formation of human umbilical venous cells. Phytother Res 2003;17(2):107-111. 12601670
  9. Kampf, R. and Steinegger, E. [Thin layer and gas chromatographic studies on oleum anisi and oleum anisi stellati]. Pharm Acta Helv  1974;49(2):87-93. 4849992
  10. Perry, L. M. Medicinal Plants of East and Southeast Asia  1980;180.
  11. Sy, L. K. and Brown, G. D. Novel phenylpropanoids and lignans from Illicium verum. J Nat Prod 1998;61(8):987-992. 9722481
  12. Tuan, D. Q. and Ilangantileke, S. G. Liquid CO2 extraction of essential oil from star anise fruits (Illicium verumH) . J Food Eng  1997;(31):47-57.
  13. Zhou, J., Lu, G., Zhong, X., and Wen, H. [Quantitative determination of anethole in the fruit of Illicium verum from various places of Guangxi province]. Zhong Yao Cai 2005;28(2):106-107. 15981881
  14. Lee, S. W., Li, G., Lee, K. S., Song, D. K., and Son, J. K. A new phenylpropanoid glucoside from the fruits of Illicium verum. Arch Pharm Res 2003;26(8):591-593. 12967191
  15. Lee, S. W., Li, G., Lee, K. S., Jung, J. S., Xu, M. L., Seo, C. S., Chang, H. W., Kim, S. K., Song, D. K., and Son, J. K. Preventive agents against sepsis and new phenylpropanoid glucosides from the fruits of Illicium verum. Planta Med 2003;69(9):861-864. 14598217




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